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Biosynthetic Pathway 7.2 Flavonoid and Hydroxystilbene Biosynthetic Pathways 7.3 Radical Coupling of Flavonoids and Hydroxystilbenes with Monolignols – Flavonolignans and Stilbenolignans 7.4 Lignin Monomers Derived from the Flavonoid and Hydroxystilbene Biosynthetic Pathways 7.5 Conclusions and Future Prospects 7.6 Acknowledgments References

      15  8 Complex Regulation of Proanthocyanidin Biosynthesis in Plants by R2R3 MYB Activators and Repressors 8.1 Introduction to PAs and Flavan‐3‐ols 8.2 Regulation of PA and Flavonoid Biosynthesis by MYB Transcription Factors 8.3 The Importance of Repressor MYBs in PA and Flavonoid Metabolism 8.4 The Complex Interaction of PA MYB Activators, MYB Repressors, and bHLH Transcription Factors 8.5 Developmental and Plant Hormone‐Mediated Regulation of the PA Pathway via MYBs 8.6 Stress Activation of PA Synthesis by MYBs in Poplar and Other Woody Plants 8.7 Summary and Conclusions 8.8 Acknowledgments References

      16  9 Conservation and Divergence Between Bryophytes and Angiosperms in the Biosynthesis and Regulation of Flavonoid Production 9.1 Introduction 9.2 Flavonoid Biosynthesis in Basal Plants 9.3 Origins of the Phenylpropanoid Biosynthetic Pathway and Conservation Across the Embryophytes 9.4 Notable Phenylpropanoids of Bryophytes 9.5 Regulation of Flavonoid Production 9.6 Concluding Remarks 9.7 Acknowledgements References

      17  10 Matching Proanthocyanidin Use with Appropriate Analytical Method 10.1 Introduction 10.2 General Proanthocyanidin Structure and Analysis 10.3 Red Wine Mouthfeel 10.4 Biological Activity 10.5 Summary References

      18  11 Imaging Polyphenolic Compounds in Plant Tissues 11.1 Introduction 11.2 The Chemical Nature and Intrinsic Fluorescence Properties of Polyphenols 11.3 Microscopy‐based Methods for Imaging Plant Phenolic Compounds 11.4 Polyphenols and Microscopy Imaging 11.5 Future Challenges and Opportunities in Imaging Plant Metabolites 11.6 Acknowledgments References

      19  Index

      20  End User License Agreement

      List of Tables

      1 Chapter 1Table 1.1 Equilibrium constants of heavenly blue anthocyanin and their deriva...Table 1.2 Rate constants betweenAH+ and CB (estimated error 10%). Reproduced ...

      2 Chapter 2Table 2.1 Results of flavan annulation.

      3 Chapter 3Table 3.1 Portfolio of mobile biodiscovery training modules used in workshops...

      4 Chapter 4Table 4.1 Representative examples of variation in CT concentration amongPopul...Table 4.2 Effects of abiotic environmental factors on CT concentrations inPop...Table 4.3 Effects of biotic environmental factors on CT concentrations inPopu...Table 4.4 Effects ofPopulus CTs on mammals and invertebratesTable 4.5 Effects ofPopulus CTs on community structureTable 4.6 Effects ofPopulus CTs on ecosystem function

      5 Chapter 5Table 5.1 Predicted and observed percentages of binary mixtures of procyanidi...

      6 Chapter 6Table 6.1 Number of PA compounds in mixtures containing two, three, or four d...Table 6.2 Proanthocyanidin (PA) concentrations and related products in feeds ...Table 6.3 Nucleophiles that have been used for depolymerization of proanthocy...

      List of Illustrations

      1 Chapter 1Figure 1.1 Sketch of the metalloanthocyanin responsible for the color in Cum...Scheme 1.1 The metamorphosis concept in biology and in chemistry applied to ...Scheme 1.2 Energy level diagram for anthocyanins and related compounds in ac...Scheme 1.3 Extension to the basic medium of Pelargonidin‐3‐glucoside.Figure 1.2 Absorption spectrum of heavenly blue anthocyanin, a peonidin deri...Figure 1.3 Stopped flow traces 4’‐hydroxyflavylium (at pseudo‐equilibrium, w...Scheme 1.4 Energy level diagram of the compound 4’‐hydroxyflavylium and the ...Figure 1.4 Representation of the mole fraction distribution of the compound

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